In this report, we address this question with a comprehensive look at public school leaders in Greater Milwaukee. Our analysis covers the four-county Milwaukee metropolitan area and uses the most up-to-date data available to answer a number of questions, including: (1) How many school leaders are there in Greater Milwaukee and how does that number compare among school districts?; (2) What are the ages and demographics of school leaders across the region?; (3) What qualifications and levels of experience do school leaders possess?; and (4) What are the advancement options for school leaders and is there mobility across districts? The education profession in Wisconsin has been the subject of much discussion and debate in recent years, particularly during consideration and implementation of Wisconsin Act 10. Consequently, our analysis includes data over multiple years to capture changes in school leader characteristics that have occurred since the 2009-10 school year. This report is the second in a series on the educator workforce in the Milwaukee area. The first report, "Taking Attendance: An Analysis of Greater Milwaukee's Teacher Workforce," found that the number of teachers in the region has decreased nearly 5% since 2009-10. [For the first report in this series, see ED570112. For the third report in this series, see ED570114 .]